The Story of Steve Jobs: An Inspiration or a Cautionary Tale?

Photo: Gregg Segal

Soon after Steve Jobs returned to Apple as CEO in 1997, he decided that a shipping company wasn’t delivering spare parts fast enough. The shipper said it couldn’t do better, and it didn’t have to: Apple had signed a contract granting it the business at the current pace. As Walter Isaacson describes in his best-selling biography, Steve Jobs, the recently recrowned chief executive had a simple response: Break the contract. When an Apple manager warned him that this decision would probably mean a lawsuit, Jobs responded, “Just tell them if they fuck with us, they’ll never get another fucking dime from this company, ever.”

The shipper did sue. The manager quit Apple. (Jobs “would have fired me anyway,” he later told Isaacson.) The legal imbroglio took a year and presumably a significant amount of money to resolve. But meanwhile, Apple hired a new shipper that met the expectations of the company’s uncompromising CEO.

What lesson should we draw from this anecdote? After all, we turn to the lives of successful people for inspiration and instruction. But the lesson here might make us uncomfortable: Violate any norm of social or business interaction that stands between you and what you want. Jobs routinely told subordinates that they were assholes, that they never did anything right. According to Isaacson, even Jonathan Ive, Apple’s incomparable design chief, came in for rough treatment on occasion. Once, after checking into a five-star London hotel handpicked for him by Ive, Jobs called it “a piece of shit” and stormed out. “The normal rules of social engagement, he feels, don’t apply to him,” Ive explained to the biographer. Jobs’ flouting of those rules extended outside the office, to a family that rarely got to spend much time with him as well as to strangers (police officers, retail workers), who experienced the CEO’s verbal wrath whenever they displeased him.

Jobs has been dead for nearly a year, but the biography about him is still a best seller. Indeed, his life story has emerged as an odd sort of holy scripture for entrepreneurs—a gospel and an antigospel at the same time. To some, Jobs’ life has revealed the importance of sticking firmly to one’s vision and goals, no matter the psychic toll on employees or business associates. To others, Jobs serves as a cautionary tale, a man who changed the world but at the price of alienating almost everyone around him. The divergence in these reactions is a testament to the two deep and often contradictory hungers that drive so many of us today: We want to succeed in the world of work, but we also want satisfaction in the realm of home and family. For those who, like Jobs, have pledged to “put a dent in the universe,” his thorny life story has forced a reckoning. Is it really worth being like Steve?

In one camp are what you might call the acolytes. They’re businesspeople who have taken the life of Steve Jobs as license to become more aggressive as visionaries, as competitors, and above all as bosses. They’re giving themselves over to the thrill of being a general—and, at times, a dictator. Work was already the center of their lives, but Jobs’ story has made them resolve to double down on that choice.

The gospel of Steve Jobs has spread far from Silicon Valley, inspiring people in every field of business.

Steve Davis, CEO of TwoFour, a software company that caters to financial institutions, was eager to talk about Jobs’ influence on his own life and career. But first he had to find a free half hour. When he finally did steal a few moments to speak, he explained that he had consciously set aside certain aspects of his family life, since he believes that startups fail when those involved aren’t committed to being available 24 hours a day. Luckily, Davis told me, he was blessed with a wife who picked up the slack.

Davis detailed these choices matter-of-factly, but his voice rose with fervor when he described the intensity and uncertainty of entrepreneurship. He loved every minute of it. He didn’t operate with a corporate safety net. His lawyer was calling him at that very moment with a contract question, and Davis needed to pick a direction and just go with it. What should he decide? He admitted he didn’t know. The thrill came from the possibility that he might be wrong. “Guys who start companies are different from other people,” he said. “We’re willing to fail. Look at Jobs. He got knocked down, and he kept going. He’s totally unconventional, driving on his particular path, and either you join him or get out of the way.”

Join or get out of the way—it’s a phrase that sums up what Jobs’ life has taught his admirers today. Andrew Hargadon, a professor at UC Davis and author of How Breakthroughs Happen: The Surprising Truth About How Companies Innovate, points out that Jobs’ brashness has helped inspire a larger reaction to several decades of conventional wisdom about the importance of worker empowerment and consensus decision- making. “Jobs is showing us the value in the old-school, autocratic way. We’ve gone so far toward the other extreme, toward a bovine sociology in which happy cows are supposed to produce more milk.” That is, it took a hippie-geek like Jobs to give other bosses permission to be aggressive and domineering again.

This isn’t aggression for its own sake but for the good of a company. Tristan O’Tierney, a Mac and iPhone software developer, helped Twitter creator Jack Dorsey found the credit-card-swiping startup Square three years ago. O’Tierney says that he now sees the value in bluntly telling people their work is crap. “You don’t make better products by saying everything is great,” he explains. “You make them better by forcing people to do work they didn’t know they had in them.” Aaron Levie, a self-described Jobs “wantrepreneur,” started Box, which allows cloud-based file-sharing, in his USC dorm room in 2005. To new hires, he quotes Jobs—”Some people aren’t used to an environment where excellence is expected”—to make clear to them that Box is just such an environment. “My lesson from Jobs,” Levie says, “is that I can push my employees further than they thought possible, and I won’t rush any product out the door without it being perfect.” He adds: “That approach comes with collateral damage on the people side.”

Are You an Acolyte or a Rejector?

Steve Jobs had a brash personality that lends itself to very different interpretations, depending on who you are. Based on these anecdotes from Walter Isaacson’s biography, which camp do you fall into? —B.A.

1

In 1975, Atari paid Jobs and Steve Wozniak to create the iconic game Breakout. Woz pulled four all-nighters to get it done—but Jobs pocketed the whole bonus that Atari paid for the game’s efficient design.

It’s true that Apple employees rarely quit when Jobs called them shitheads, or even when he took credit for their ideas. An early manager on the Mac team told Isaacson about the abuses Jobs heaped on employees. But she said, “I consider myself the absolute luckiest person in the world to have worked with him.” These sorts of testimonials are the proof, for many entrepreneurs and executives, that strong leadership and impressive results will lead employees to tolerate, even to embrace, unpleasant work conditions. Ray Dalio, founder of Bridgewater Associates, the world’s most profitable hedge fund, has been called the “Steve Jobs of investing,” in part because his firm practices a form of radical forthrightness. All Bridgewater employees are expected to clash with one another, to speak without filters or concerns about sensitivities. Dalio says he shares Jobs’ belief in the benefits of a tough, brutally candid office environment, though he requires his employees to dish it out to him just as much as they take it. He likens the mode of dialog he practices—not just at Bridgewater but in all his personal relationships—to twisting one’s limbs into a difficult yoga position or training as a Navy SEAL. “Pretty soon the pain becomes pleasure and you can’t live without it,” he says.

What acolytes want most of all is to possess the same certainty about their vision that Jobs felt about his. Neal Sales-Griffin, 25-year-old cofounder and CEO of Code Academy, a programming school in Chicago, says that after studying Jobs’ life, he doesn’t waste time anymore with the intricacies of etiquette. He openly denigrates projects that aren’t working, even if others have already invested countless hours in them. He recalls Apple’s inauspicious launch of MobileMe, the subscription service that was supposed to sync a user’s entire online existence in the cloud. From a stage in an Apple auditorium, Jobs berated the MobileMe employees for their inability to create a better product—”You should hate each other for having let each other down”—and then fired the team leader on the spot. “Jobs’ passionate approach has empowered me to be myself, with my flaws and difficulties and limitations,” Sales-Griffin says. “Look what came of it for him.”

The second camp is what you might call the rejectors. These are entrepreneurs who, on reading about Jobs since his death, have recoiled from the total picture of the man—not just his treatment of employees but the dictatorial, uncompromising way that he approached life. Isaacson’s biography is full of stories of Jobs as an unpleasant individual—the fits he would throw over the most picayune-seeming details, like the type of flowers in his hotel room or the way an aging Whole Foods barista made his smoothie. He would park in handicap spaces; he refused to get a license plate for his car. And he abandoned his oldest daughter, applying his “reality distortion field” to the question of his own paternity.

Jeff Atwood was once an acolyte. He had subsumed the whole of his identity into the company he created: Stack Exchange, a network of online Q&A sites. “You gird for war,” he says about the ethos of running a startup. “You need a spiritual fervor, an almost religious belief in the mission, to throw yourself on the shores and attack.” So it came as a surprise to Atwood—and everyone else—when he realized that he had to leave behind Stack Exchange and the startup life. And the Isaacson biography was what prompted his epiphany, turning him into a devout rejector.

He already knew all the stories about Jobs the businessman and innovator. But what he found harrowing, almost too painful to read, were the details about Jobs’ family and personal life. Atwood was brought to tears by a passage in which Jobs showed drawings for the new Apple campus to his son at home one night, and it didn’t even occur to him to call over his daughter, who had expressed interest in becoming an architect. “He paid less attention to Erin,” Isaacson writes about Jobs and his daughter, “who was quiet, introspective, and seemed not to know exactly how to handle him, especially when he was emitting wounding barbs.” Atwood, 41, recently became a father to twin daughters, and he said what Jobs did was “the opposite of parenting. Parenting is being there, man. It’s showing up.” The biography forced him to see that he, like Jobs, had allowed work to dominate his life. Atwood groaned as he recalled how Jobs would respond directly and rudely to some random customer’s email in the middle of the night: “Here’s why you’re an idiot.” Atwood would do the exact same thing. He really didn’t want to quit, but he saw that nuclear option as the only way to disrupt the cycle. “If you’re going to fail at building something,” he says, “fail at building the fucking iPad. Don’t fail at building children.”

For some of these more repulsed readers, it’s the tales of managerial cruelty that have gotten under their skin. Verinder Syal—a former executive at Quaker Oats who bought a coffee franchise, sold it, and now runs a consulting firm and teaches business-school students—expected to adore the biography. He greatly admired Jobs’ ambitions, and he regularly extolled him to students as a paragon of leadership. The book saddened him, though: Syal couldn’t understand why Jobs felt the need to be right all the time and to blame others, why he had to claim other people’s ideas as his own. Syal says he went back to his classes and admitted that he was wrong. “Jobs was like dynamite,” Syal says. “Dynamite clears paths, but it also destroys everything around it.” Syal didn’t think much of Bill Gates before, but he does now. “Gates evolved from an asshole into a human being,” he says. “Jobs remained an ass.”

To some, the Steve Jobs story reveals the value of sticking to one’s vision. To others, it’s a study in cruelty and alienation.
Photo: Gregg Segal

But most of the rejectors are, like Atwood, entrepreneurs who worry about their roles as fathers. A few of them single out one particular moment near the end of the book, when Jobs explains why he asked Isaacson to write it. “I wanted my kids to know me,” Jobs said. “I wasn’t always there for them, and I wanted them to know why and to understand what I did.” Brad Wardell, CEO of the software and computer-game-design company Stardock, was shaken when he realized that the same powers of reality distortion that allowed Jobs to create the iPod also led him to deny the seriousness of the pancreatic cancer that killed him. (For nine months, Jobs delayed undergoing conventional treatment.) Wardell, 41, says his formative years corresponded to the rise of Jobs, and Jobs’ influence helped him “put every ounce of energy and focus into Stardock.” That translated into 80- and 90-hour workweeks, maniacally testing every version of every piece of software, reviewing all source code, writing notes nonstop. “But I realized that, like Jobs, I could die. Jobs missed out on his kids, and I’d have missed out on mine too.” Wardell now often works from home, and he has hired people to manage aspects of the business he previously handled himself.

Many of these former fanboys are reconsidering their allegiance to Jobs in part because they are no longer boys. Now in their forties, they’re confronting the end of their young-adult selves—they have children, and their own parents have become senior citizens or died. Matt Haughey, founder of the community weblog Metafilter, addresses this point directly in a presentation called “Lessons From a 40- Year-Old,” which he delivered last February at the web-design conference Webstock. Haughey remarked that he was grayer, his daughter was turning 7, he had recently put down a longtime pet, and he had experienced his own near-brush with cancer (a brain tumor that turned out to be benign). Haughey heard many in his cohort—most of them devoted Jobs followers—saying, “It is time not to end up like Steve.” So rather than trying to create the next Apple, he proposed building a “lifestyle business,” a smaller-scale enterprise that rejects venture capital and funds itself, leaving its owner time for pursuits outside of work. He displayed a graph of his mid-twenties existence, with the bar representing work towering over the one for personal life. Now that he’s 40, the bar heights are reversed.

It’s worth pointing out that these male rejectors have wound up where most female entrepreneurs have been all along. Women CEOs and managers didn’t need a biography of an absent father to start thinking about balancing work and family; unlike the fortysomething dudes, they’ve been having conversations about this trade-off most of their lives. Rashmi Sinha, CEO of the presentation-sharing service SlideShare, was pregnant with twins when she devoured the Isaacson book. She read it to understand how Jobs created great products, but the possibility of gleaning any personal lessons from his life didn’t even cross her mind. Similarly, Heidi Messer, cofounder of the affiliate-marketing firm LinkShare, has told her entire marketing staff to read the biography, but without any thought that they’d construe Jobs to be her own role model as a manager. She does suggest one personal lesson from Jobs’ life: “If he could do Apple and Pixar—two multibillion-dollar companies—then I should be able to handle one business and also my family.”

The rejectors all know that quelling their Jobs-like tendencies will be a struggle. They are by nature strivers, perfectionists. They also know that their retreat from the struggle—adopting a lifestyle-centric approach to business—means they will never accomplish as much as they would have otherwise, let alone as much as Jobs did. If they used to release six products a year, now they produce only two. If previously they sent out three dozen emails during the dinner hours, then now they make do with sending just a few. Rather than planning to take their startups public, they are shooting for enough profit to sustain their employees and themselves. To create the lifestyle they want, or need, these entrepreneurs are reining in their compulsions, imposing limits on themselves.

When he’s not writing best-selling biographies, Walter Isaacson runs the Aspen Institute, a nonpartisan think tank based in Washington, DC, that covers everything from business development to education and foreign policy. At his office there, Isaacson proves to be a gracious New Orleanian, easeful and attentive—in short, nothing like Steve Jobs. He says that readers of the biography have been seeking him out to discuss their uncanny similarities to Jobs or their desires to behave more like him. Two executives visited the writer separately just hours before me. One of them was Bridgewater’s Dalio, who came specifically to confer about people he called “shapers,” those who overcame tremendous opposition to transform vision into reality. Dalio hoped that he and Isaacson could suss out a few of the traits shared by such shapers as Jobs, Benjamin Franklin, Albert Einstein, Margaret Thatcher, and perhaps also Dalio himself. When I asked Isaacson about the life lessons of Jobs, he ducked behind his desk and returned with articles that had recently been forwarded to him, each one about the merits and demerits of emulating Jobs’ jerkiness.

Isaacson himself has published what he deems a corrective, writing in Harvard Business Review that readers hoping to draw meaning from Jobs’ life should fixate less on his petulance as a boss and more on his remarkable achievements at Apple and Pixar. Isaacson distilled the real leadership lessons of Steve Jobs down to 14 business proverbs, such as “Bend reality,” “Push for perfection,” and “Tolerate only A players.” “Long after their personalities are forgotten,” he remarks of Jobs, along with the pantheon of Edison, Ford, and Disney—not one a saint—”history will remember how they applied imagination to technology and business.”

The author admits that he now tends to defend Jobs against personal attacks, since his book has provided much of the ammunition. Isaacson sees Jobs as being hardly more blameworthy, even in his worst moments, than other powerful people. Readers he knows personally claim to be shocked that Jobs would brazenly park in handicap spaces, but Isaacson says some of them are bankers who created the derivatives that screwed clients out of their life savings and helped lead to worldwide recession. When other readers express their contempt for the way Jobs treated his family, Isaacson asks them, “Then how come you’ve been married three times and this particular daughter doesn’t fucking speak to you?” Indeed, Isaacson rejects the premise that Jobs failed with his family. He points out that Jobs ended up with a strong marriage and four loving children, all of whom were at his side during his illness. A wooden table filled much of Jobs’ kitchen, and for the last two decades of his life he came home just about every night and sat down for dinner. “Jobs could have been a better father,” Isaacson concedes. “But I look at that family, and it’s perfectly wonderful. It couldn’t be a better family.”

Yet Isaacson understands how genius worship has led to multiple interpretations. “It’s like arguing the gospels with a fundamentalist,” he says about the futility of trying to rebut what he sees as misreadings of Jobs’ life. He tells me what he’s told lots of people who have sought him out to catechize about the book—that his biographies aren’t how-to manuals for the good life. He isn’t arguing that readers not look for guidance in the story of Jobs; he knows it is the nature of biography-reading to do so. But Isaacson stresses that Jobs’ life was complex, the lessons to be found myriad.

At least since Plutarch illuminated the moral character of famous Greeks and Romans, readers have looked to biographies for guidance and inspiration. My father still recites a corny Longfellow poem he learned as a kid back in the ’50s:

Lives of great men all remind usWe can make our lives sublime,And, departing, leave behind usFootprints on the sands of time;

Some intimate portraits are meant to debunk the iconic figure, their anecdotes served up as exposé. But usually the readers of biographies are supposed to recognize some aspect of themselves, or a wished-for better self, in the footprints of the eminent subjects. The genre is intensely individualistic, rebuffing sociology and collective history, and the reading experience winds up being no less personal.

Ironically, in Jobs’ remarkable story of self-creation we can see why the rest of us are so hungry for a role model to light our own paths. Whether it was in the early days, when he manipulated Steve Wozniak into building products for him to sell, or later in his career, when he was struggling to shape NeXT from scratch, or even after returning to Apple, when he created entirely new products, Jobs had no one to tell him how to realize his vision. He made high-stakes decisions on his own, with little to rely on besides his well-honed intuition. And on a smaller scale, isn’t that true of us all? In life, as in business, there really aren’t any concrete answers or clear guides. We can’t help but see a biography like Steve Jobs as a rare road map to the uncharted world we awake to every morning.

So what, then, is Jobs’ real legacy as a human being? “It’s his passion,” Isaacson says, after some deliberation. “We all want to lead the passionate life. We want a life of emotional connections. If that’s what you get by saying, ‘I will be more like Steve Jobs,’ then that’s not bad.”

The gospel of Steve Jobs has spread far from Silicon Valley to touch people in every field of business. My cousin Jason is a yoga entrepreneur in Asheville, North Carolina; he makes foam accessories to help people stretch more ergonomically. When he came to visit not long ago, he brought his copy of Steve Jobs along with him. “I care about all these tiny design details no one else does,” he says, nodding at the book as it sat between us on my dining room table. “I get frustrated, catching myself telling people who work for me that their ideas are shit.” Our respective children in the next room celebrated their reunion by putting on a succession of princess and monster costumes. Motioning toward them, Jason said he now accepts that traveling constantly and spending less time with family is a necessary trade-off if he, too, wants to produce a great product. “When your karma and your lila meet, you find your dharma—your one true path,” he tells me, citing a precept that might have sat well with Jobs, a devotee of Eastern religions. “It’s a beautiful concept. You discover your way to contribute to the world. That’s what Jobs found. He contributed so much to humanity with his products.”

In the end, that remains the paradox in the life of Steve Jobs. He put his uncompromising and sometimes brutal personality into the creation of products that strike us as beautiful, even uplifting. But the historical moment that he helped to create—a magical intersection of technology and commerce and culture, as our computers and computerized gadgets matured from purely functional items to expressions of ourselves—is unique to his life story. Without his unyielding approach to design, we might never have had our iPods and MacBooks and iPads. But most of us don’t need, or want, to take such an unyielding approach. We don’t operate Apple-sized corporations and redefine industries. Our employees, if we have any, will quit or undermine the company if they are repeatedly called shitheads who suck. Family members will find ways to administer payback if persistently ignored or mistreated. Jobs operated on an entirely different plane from just about anyone else. For the rest of us, trying to behave like him will make us and everyone around us miserable.

As he was writing his 2007 book, The No Asshole Rule, Robert Sutton, a professor of management and engineering at Stanford, felt obligated to include a chapter on “the virtues of assholes,” as he puts it, in large part because of Jobs and his reputation even then as a highly effective bully. Sutton granted in this section that intimidation can be used strategically to gain power. But in most situations, the asshole simply does not get the best results. Psychological studies show that abusive bosses reduce productivity, stifle creativity, and cause high rates of absenteeism, company theft, and turnover—25 percent of bullied employees and 20 percent of those who witness the bullying will eventually quit because of it, according to one study.

When I asked Sutton about the divided response to Jobs’ character, he sent me an excerpt from the epilogue to the new paperback edition of his Good Boss, Bad Boss, written two months after Jobs’ death. In it he describes teaching an innovation seminar to a group of Chinese CEOs who seemed infatuated with Jobs. They began debating in high-volume Mandarin whether copying Jobs’ bad behavior would improve their ability to lead. After a half-hour break, Sutton returned to the classroom to find the CEOs still hollering at one another, many of them emphatic that Jobs succeeded because of—not in spite of—his cruel treatment of those around him.

Sutton now thinks that Jobs was too contradictory and contentious a man, too singular a figure, to offer many usable lessons. As the tale of those Chinese CEOs demonstrates, Jobs has become a Rorschach test, a screen onto which entrepreneurs and executives can project a justification of their own lives: choices they would have made anyway, difficult traits they already possess. “Everyone has their own private Steve Jobs,” Sutton says. “It usually tells you a lot about them—and little about Jobs.”